Michael Caine: The Man Who Would Be Dear Dictator

Michael Caine and Sean Connery in The Man Who Would Be King. Columbia Pictures

Between Play Dirty, Get Carter, Dirty Rotten Scoundrels, The Muppet Christmas Carol, Children of Men and The Last Witch Hunter, it would be tricky to pick my favorite Michael Caine role, except for the existence of Peachy Carnehan in The Man Who Would Be King. Director John Huston tried for two decades to adapt Rudyard Kipling’s novella, at one time or another roping in famous actors like Clark Gable, Humphrey Bogart, Kirk Douglas, Burt Lancaster, Richard Burton, Peter O’Toole, Robert Redford and Paul Newman before finally filming with Caine and Sean Connery for the roles of Peachy and Danny, two swindlers navigating the imperial machinery of the British Raj.

An Englishman and a Scot, each perfect at conveying both the regal and sleazy elements of the adventure tale, their characters’ British charm and can-do just barely masking the selfishness that brings them to ruin. Convinced India has been too thoroughly exploited by those richer and better connected than them, Peachy and Danny set out through Pakistan and the Khyber Pass to Kafiristan, a mountain-bound kingdom last conquered by Alexander the Great (at least in Kipling’s semi-mythical telling). Between their self-confident swagger, soldiering skill and a handful of lucky religious miracles, Danny becomes king of Kafiristan, Peachy his reluctant vizier. But like all misbegotten power, it can’t last.

In its first trailer, Caine’s new movie, Dear Dictator, takes a very different approach to the perils of dictatorial power. Caine plays Fidel Castro a “British-Caribbean dictator” who flees his island nation and moves in with his pen pal, high school rebel Tatiana Mills (Odeya Rush). Using his magical dictator personality secrets, Rush’s character will overthrow the school’s mean girls, get the guy and rule the school.

Though the premise sounds like it was pulled from Sacha Baron Cohen’s trashcan, the tone of the Dear Dictator trailer is closer to something starring a talking animal. Part of me wants to get really offended, maybe bring up the 68,000 people the U.S. helped murder during Operation Condor. There was plenty of waterboarding (or milkboarding, as Dear Dictator would have it) going on in Cuba, but it sure as hell wasn’t the communists doing it. But no matter how grating it is when we impute our own crimes in South America to the leftist leaders we’ve conspired to overthrow, Dear Dictator doesn’t look like the CIA’s most effective propaganda vehicle (that would be Zero Dark Thirty).

Instead, Dear Dictator just looks like garden-variety American rapaciousness: triumph of the will, ends justify the means, etc. As the trailer says, “His methods might be unjust… but his heart’s in the right place,” perfectly summarizing excuses made for everything from Bill Clinton bombing pharmaceutical factories in Sudan to George W. Bush’s Iraq War to Barack Obama drone-bombing Yemeni weddings.

In The Man Who Would Be King, Caine’s character was the one to see the writing on the wall, who knew that all the lies and the conman routines and the swagger would crumble under the demands of power. On March 16, in theaters and VOD streaming, Dear Dictator will give Caine the chance to rebut his 1975 classic.

“You must have the courage to do what you believe in, even if it hurts the ones you love,” Caine’s dictator teaches us. This will probably be softened; Tatiana will learn some valuable counter-lessons after alienating her friends and family. But her victory over high school will taste just as sweet, another classic imperialist trope: you can keep the goods, as long as you make apologetic gestures and self-reflect. Not true, says Caine in The Man Who Would Be King, you can jockey for position, step on the backs of your fellows, but no matter how much you pillage, you can’t take it with you.